1,2-Dichloroethane → N-(3-nitrophenyl)acrylamide

HRID 1815891Notes

Reaction equation

HRID 1815891 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:34](O)(=[O:37])[CH:35]=[CH2:36]>C(Cl)Cl.CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:34](=[O:37])[CH:35]=[CH2:36])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6581Acrylic AcidHCID 74233-NitroanilineHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 12531248N-(3-nitrophenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Nitroaniline (2.0 g, 14.48 mmol) was dissolved in CH2Cl2 (75 ml) and cooled to 0° C. To this solution were added EDC (8.3 g, 43.4 mmol), HOBT (5.9 g, 43.4 mmol), DIEA (12.6 ml, 72.4 mmol) and acrylic acid (3.97 ml, 57.9 mmol). The reaction mixture was kept at RT for 1.25 h. The reaction mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography using 1:1 EtOAc/hexanes as the solvent to give N-(3-nitrophenyl)acrylamide.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-27c98a037da64f22bf6e9137ce025195
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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